Hydrogen Bromide → JWH 018 5-hydroxyindole metabolite
Reaktionsgleichung
Br.C[O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:8]=[C:7]2[C:18]([C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1)=[O:19]>O>[OH:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:8]=[C:7]2[C:18]([C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1)=[O:19]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of hydrobromic acid (48 w/w/%) in water (150 ml) was added 5 (6.5 g, 17.5 mmol) and the mixture was heated at reflux for 3 h. The solution was cooled to room temperature and concentrated to dryness. Water was then added (200 ml), the solution neutralized to pH 7-8 and then extracted with ethyl acetate (3×150 ml). The combined organic layers were washed by water (150 ml), brine (150 ml), dried over Na2SO4, filtered and concentrated to dryness. The crude product was then recrystallized from ethyl acetate/hexane to give a white solid of 5-hydroxy-3-(1-naphthoyl)-N-pentyl-1H-indole 6 (4.5 g, 72%).